


Uphill Battle

by Zana_Zira



Series: Before They Were Brothers Again [2]
Category: Supernatural
Genre: Big Brother Dean, Canon Compliant, F/M, Grief/Mourning, Grieving Sam, POV Dean Winchester, POV Jessica Moore, Pre-Series, Protective Dean Winchester, Sneakiness, Stanford Era
Language: English
Status: Completed
Published: 2014-03-25
Updated: 2014-03-25
Packaged: 2018-01-16 22:45:29
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 4,933
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1364506
Author URL: https://archiveofourown.org/users/Zana_Zira/pseuds/Zana_Zira
Summary: <blockquote class="userstuff">
              <p>It wasn't supposed to involve her. Things between the Winchesters never involved Jessica Moore – Sam had made that clear in the two years they'd known each other. But something hadn't been right with Sam since his twenty-first birthday, and she wasn't about to just stand by and watch him fall apart.</p>
            </blockquote>





	1. Part I

**Author's Note:**

> Disclaimer: Supernatural and its characters are the property of Eric Kripke. Sadly, I do not own any of these guys.
> 
> A/N: This will be posted in two parts, the second of which will tie this into the end of the pilot episode. Enjoy!

It wasn't supposed to involve her.

Things between the Winchesters never involved Jessica Moore – Sam had made that abundantly clear in the two years they'd known each other. "It isn't anything personal," he always said, "I'm just not comfortable talking about it." So she always stayed out of Sam's family issues, letting him deal with his inner demons alone and at his own pace. That was how he wanted it, and she respected that. After all, who didn't have a few skeletons in the family closet that they hated to talk about? If he had a few more than most, well, that was his business. All she cared about was that she loved him, and he was hers. And if he ever decided he wanted someone to vent to about his family, she would always be there for him.

But ever since his twenty-first birthday, three days ago, something had changed in Sam. To most of the people on campus it would have gone completely unnoticed, but Jessica was not just one of the people on campus. She sometimes knew Sam better than he knew himself, and even the smallest changes affected her almost as much as they did him. She could always sense when he needed space, or someone to be by his side and help ease the burden of being an independent young adult paying his way through one of the most expensive schools in the United States. She knew when the stress of school was getting to be too much for him by the way his hands would slowly make their way to his temples, trying to massage away the forming headache and failing every time, and then she would force him to bed with a cup of hot tea and remind him that law school would still be there when he woke up. She could tell when he was happy or sad or scared, just from the tilt of his eyebrows or the tiny wrinkles that would appear around his eyes when he was focusing too hard on something. Jessica could always tell.

So now, she could tell that Sam wasn't feeling like his usual self. The tan-colored cast that covered his right leg from hip to toe was heavy and cumbersome, significantly limiting his range of movement and making it hard to balance on his one functional, and extremely long, leg. The plaster made him hot and sweaty and itchy, driving him crazy until she would hand him a clothes hanger to at least scratch the bottom of his foot – until the stitches came out, though, he unfortunately wasn't allowed to scratch near the surgery site. The hospital wasn't used to dealing with men of Sam's size, so the largest crutches they had didn't quite fit. She could tell he hated wobbling around on crutches that even at their largest possible size were too short for him, even if he didn't complain. To hate being slow and vulnerable was perfectly understandable for an independent guy like Sam, so it was not what worried her. A vulnerable Sam was usually still a slightly clingy Sam, embarrassed about needing help but grateful for it anyway.

This Sam was not clingy; he was distant, quiet, and a little cold.

Even if he didn't seem as bothered by the inconveniences of a broken leg as she had expected, something was definitely wrong. A slight shadow hung low under his hazel eyes, making him look tired and much older than his mere twenty-one years. He sighed more than usual, too, staring off into space when he thought she wasn't looking, and his temper had shortened to the point of making him constantly snappish and irritable, although never with her. All of this added up to one thing in her mind: whatever Sam's brother had said to him on his birthday, it hadn't been good.

She'd seen the caller-ID at the same time Sam did, and she'd seen how his face fell further with each word he read. She had meant to ask him about it once they got home from the restaurant, but then he had taken that terrible fall and scared all thoughts of Dean out of her head. Only now, as she sat watching Sam staring listlessly at the clock on the far wall, did she remember the text message from his brother; the text message that, given the fact that his phone had been crushed under his weight when he fell, would probably remain hidden from her forever unless Sam decided to tell her what it had said. That, though, was about as likely as finding snow in southern California in the middle of summer.

No. If she wanted answers, she was going to have to find them for herself.

"Sam?" she asked quietly, sitting down beside him on the couch and frowning when he barely moved his eyes away from the clock to glance at her. He looked depressed, plain and simple.

"I'm going out to get some groceries and pick up your prescriptions from the pharmacy. You want anything special?"

Sam smiled softly, leaning over to give her a quick, chaste kiss and wincing when he put a little too much of his weight on the cast. "I already have you, don't I?"

Jess laughed and kissed him back, kneeling down and lifting his cast up so he could pivot around to lay it on a pillow she had set at the other end. "You're such a suck-up. Alright, so if I pick up Chinese will you eat it? The new meds the doctor gave you haven't made you sick again, right?"

Sam grimaced, remembering how hellish his first night home had been when he'd spent it alternating between agonizing throbbing in his leg and relentless nausea caused by the pills meant to stop his pain. By the time he'd managed to stop vomiting long enough to realize his leg didn't hurt anymore, he'd been too tired and weak to haul himself off of the bathroom floor. If Jess hadn't been there to help him the entire time, he had no idea what he would have done.

"Yeah, that sounds fine. Just pick up whatever looks good and I'll eat it too."

"Alright. Behave yourself while I'm gone, 'kay?"

"Aww. I was planning a huge party for the second you left. Guess I gotta call it off now."

"Smartass," she said with a laugh, kissing him one more time before grabbing her purse and keys from the end table. "See you later, Sam."

"Bye, Jess."

* * *

Jessica felt a little guilty about keeping her real intentions from Sam. Or maybe more than a little. But she knew if Sam caught on to what she was about to attempt, he would either be angry, find a way to stop her, or retreat farther into himself than he already had. None of those were acceptable options, and if she lost Sam's trust in her she wasn't sure what she would do.

In spite of that, though, she continued on to her destination, pulling smoothly into the parking lot of the local Verizon store. Sam had bought his old phone here, a Palm Treo that he loved and carried everywhere, and it wouldn't be too expensive to replace on his current phone plan. When she had talked to the cashier, explained the situation, and given enough of Sam's information to prove that she actually knew him, it was remarkably easy to get him a brand new phone. She thanked the man, paid for the new phone, and then took it out to her car, sitting in the front seat and cradling the tiny device in her palms as if it might explode at any moment.

This was a great opportunity to do a little investigating into what had happened with Sam on the night he turned twenty-one. All she had to do was find his brother's phone number, give him a quick call on Sam's phone, and then delete the record from the call log. Simple, fast, efficient.

So then why was her heart racing so badly right now?

Her hands shook as she scrolled down the list and found "DEAN," hitting the little green phone button and listening to it ring. She could hear her heartbeat getting louder, pounding out the seconds while she waited for the call to go through. It continued to ring for nearly a minute, and her hope began to fade. Maybe he wasn't around his phone? Or it was on silent? Or even worse, he thought it was Sam and wasn't going to answer because of that.

She was about to end the call and try dialing the number from her own cell when she heard a tiny mechanical click, followed by a gruff "Sam?"

For several seconds she didn't know how to answer. If this was Dean, he didn't sound like she had thought he would. His voice was deep, and a little rough, and even in that one word there was a trace of an accent a little more Southern than she was used to hearing in California. Still, he sounded alert, even worried, and she immediately got the sense that whoever this Dean was or what he might have said, he still cared about his little brother. An odd thing to think, really, considering she was calling to ask what he had done to hurt Sam just three days ago.

"Sam? You there?" Dean asked, a little louder this time.

Well, no choice but to answer now. She hoped she hadn't made a mistake in calling this man.

"No, I, um… I'm not Sam. But you're Dean, right?"

"Where's Sam? Why are you using his phone?" Now the voice was harsh, guarded, and all the compassion hidden underneath only seconds ago had vanished.

"My name's Jessica Moore. I'm Sam's girlfriend."

She could almost hear him processing that on the other end, and then:

"So why are you calling on his phone?"

"He… doesn't actually know I'm calling you. I wasn't sure I should, but –"

"So then what are you calling for? Did something happen to Sam? Is he okay?"

_One question at a time, Buddy…_

"Sam's doing better. He fell down some stairs three days ago, broke his leg badly enough to need surgery, but he's getting around alright now and he's got some pretty good pain meds."

Dean's groan was barely audible but definitely there. "Aw, Sammy… What'd he do? You said three days ago – was he drunk?"

Jessica grimaced. Here was the part she'd been hoping to avoid.

"Well, not exactly. See, he uh… You…"

"Me? What the hell have  _I_  got to do with this?"

"Okay, here goes. We were out eating at a diner that was on the second floor of its building. Everything was great, Sam had enough beer to get tipsy but not drunk. And then his phone went off, and I noticed the caller-ID said 'Dean.' He read it, and he just got whiter and whiter while he did. Then all of a sudden he just stood up and walked out of the restaurant, saying we had to go home and he'd tell me what it was about later. Before I could catch up to him he fell backwards down the metal stairs, and… Well, I already told you about his leg."

When Dean was silent on the other end, a spark of fury rose inside her and she got a little bolder.

"Well? Aren't you going to say something? Your brother falls down the stairs because you said something terrible on his birthday and you don't have anything to say for yourself? What kind of asshole are you, huh?"

"Jessica, wait, I –"

"I mean, seriously, I knew Sam didn't like talking about his family, but I had no idea that  _this_  was why! Who  _does_  things like that? I thought my mom and my aunt were mean to each other, but this must really have been bad to rattle someone like Sam, and –"

"JESSICA!"

"What?!" she snapped.

"Just… hold on a second. What in the hell are you talking about? I tried all damn night to send Sam a birthday message from Florida, and it got bounced back every time. He never got anything from me."

"What time did you send it?" she asked slowly, a few things starting to slide into place in her mind.

"A little after one a.m., why?"

"Sam's phone got broken when he fell on it. That was a little after seven p.m. I just got him a new one, so he hasn't been receiving any calls or texts until now."

"Okay. Well do you know what that mystery text said?"

"I don't know. The store couldn't recover it for me and he didn't show it to me before the phone got smashed."

"Dammit. Okay, well I'm gonna try to call him later tonight. See if I can work this out."

"Good. I can tell him you're calling, so –"

"No," Dean cut in hurriedly. "Don't do that. Sam's got a huge independent streak, and he'll be beyond pissed if he thinks you're meddling in his family life behind his back. You sound like a nice girl, so just trust me when I say you don't want to get involved in this. I'll fix it, okay? But if we ever end up seeing each other in person around Sam, we've never met until that moment. Understand?"

"Got it. I'll get this phone home to Sam. Good luck, Dean."

"Thanks. Bye, Jessica…"

"Jess."

"Right. Bye, Jess."

The call ended abruptly, and Jessica sighed, slipping the phone back into its box after deleting any evidence that Dean had ever been called. She didn't know why, but she had a sinking feeling that this wasn't going to be resolved as easily as Sam's brother made it sound. Either way, she'd done all she could. Now she would just have to take care of him and wait for Dean to do the rest.


	2. Part II

**Notes for the Chapter:**

> Disclaimer: Supernatural and its characters are the property of Eric Kripke. Sadly, I do not own any of these guys.
> 
> A/N: Here it is, the part I was most looking forward to writing for so long. It also has the potential to fit into the canon if you want it to. Enjoy!

It should never have happened like this. Never. Jess was supposed to be safe. Sam was supposed to be normal, on the path to law school and living the American dream. But now everything was gone, taken away in a rush of fire before anyone could do anything to stop it. Now both brothers stood in the middle of an enormous cemetery, watching as a casket was lowered into a freshly dug grave that should have held someone much older than Jessica Moore.

Dean waited silently a few yards behind Sam, giving his little brother the space he needed but staying near enough to swoop in and take him out of there the instant Sam indicated that he couldn't handle it anymore. The coat of his hastily-bought black suit was too big, and the bunching material shifted uncomfortably beneath his tie and made his neck itch. He was sweating slightly underneath the cheap fabric, thanks to Palo Alto being sixty-five degrees even in November, but he didn't complain; whatever discomfort he felt outside must be tenfold for Sam on the inside.

The memorial service had been held on campus, so there were few people standing here now. Sam and Jessica's parents and extended family seemed to be the only ones, as a matter of fact. Sam watched, stone-faced, as Jessica's casket was finally deposited in the ground and the cables holding it were removed. Ironic, Dean thought, that they would bother to pay for a casket and bury it empty. There had been nothing left of Jessica but ashes, not even bones. The hottest fire anyone around here had ever seen, the firemen said.

" _No shit,_ " Dean thought with a disgusted shake of his head. " _Natural fires can't burn anywhere near as hot as these two did._ "

He saw Sam lift his arm up and cough into the sleeve of his suit, and his concern for his brother reared its head yet again. He'd had that cough ever since Dean pulled him away from the fire, which was to be expected after being exposed to so much smoke. The only problem was that Sam wasn't taking care of himself. He hadn't eaten once since the fire, had barely slept except when he simply became exhausted enough to slump over for an hour or two in whichever uncomfortable motel chair he was sitting in. If it hadn't been for Dean pushing him into the bathroom and telling him he reeked, he wasn't even sure the kid would have showered on his own yet.

He wanted to get Sam out of there right-the-hell-now and make him get some much-needed sleep, but he knew his brother wouldn't take kindly to that kind of treatment. So he lingered in the background, waiting for any sign that his little brother needed his help.

It was a shame, he thought. Jessica was such a nice girl. When she had picked up the phone and called him a little over a year ago, he had been able to tell immediately how much she loved his brother. It made him happy to know someone was taking care of Sammy even when he couldn't, and she'd kept her word about not mentioning the call to his brother, even when Sam continued to reject Dean's phone calls for the next year and a half. In fact, she acted genuinely surprised when she met him just before he took Sam away for a hunt in Jericho – although that could also have had something to do with him breaking into their apartment in the middle of the night. Either way, she'd never interfered in their issues after that, and he was glad.

Dean had actually come up here to apologize to Sam in person, finally getting tired of him not answering the phone and wanting to repair the fragments of a relationship that still remained between them. Dad was missing, maybe dead, and if that was the case then Sam was the only family Dean had left. He wasn't about to give up on the kid he'd practically raised, no matter how Sam's refusal to acknowledge him for the last two years might have hurt. He wished the circumstances were better, but he knew that now of all times, Sam needed to know he wasn't alone.

After the grave was filled in and flowers were placed around it, everyone knelt to pay their last respects and then began to disperse. Sam spent a few minutes talking to Jessica's parents, noticeably tensing when they hugged him and patted his shoulder. Dean could practically hear the "It isn't your fault," and "She loved you so much, Sam," coming from their lips, tired clichés that were meant to be comforting and yet would undoubtedly hurt his little brother even more.

Finally Sam managed to break away, wandering toward Dean with the same robotically controlled expression he'd been wearing since he declared that they had work to do and walked away from the burning apartment. He nodded slowly, barely acknowledging Dean, and climbed into the passenger seat of the Impala without a word. Dean sighed. He hated chick-flick moments, he really did, but this was going to have to be talked about and  _soon_. It wasn't healthy to bottle everything up the way Sam was doing, and it was either going to have to come out or eventually kill him. Option two was not even on the table.

When they reached the motel, Sam got out of the car and unlocked the door to their room, stepping inside and shedding his coat and tie as he walked. Without a word to Dean he slumped onto the bed, face buried in the pillow. His shoulders hitched once, and Dean forced himself not to cave in and give him a crushing hug. But then he relaxed, his body giving in to exhaustion, and the older hunter left him alone. Sam needed his rest, after all, so he'd let him sleep just a little while longer.

* * *

Dean was warming up a soggy leftover cheeseburger in the motel room's dirty microwave when Sam finally began to stir. It was subtle at first, just a twitch of his fingers and a tiny groan, and it looked for a while as if he might just fall asleep again. Then he suddenly jolted up in the bed, panting and gasping until he set off a coughing fit that had Dean at his side in an instant, offering him a glass of water and keeping a steadying hand on his shaking back until he could breathe properly again.

"Th-anks," he croaked, taking a few sips of water and clearing his throat.

"You good now?" Dean asked gently, patting him on the back a couple of times for good measure and trying not to be offended by the way Sam pulled away from him and nodded silently. "You hungry or anything? I can reheat some leftovers, or go get some takeout or something."

"No," Sam said immediately. "I'm not hungry."

"Sam, you haven't eaten since –"

"I know. But I'm not hungry."

Dean sighed, running his fingers back through his spiky hair. "Sam, please. You're not taking care of yourself at all and I'm starting to worry a little bit."

"Well don't. I told you I'm fine and I meant it." He stood up from the bed, wobbling a little before he got his bearings, and stared hard at Dean. "Besides, since when have I needed you to worry about me? I made it fine on my own for almost four years without you hovering over me."

"Yeah, and look how well that turned out!" Dean spat. Sam's eyes widened a fraction of an inch and Dean mentally kicked himself, not having intended to say anything like that to his already grieving brother. "Crap, that's not what I meant, Sammy."

"Yeah, I'll bet," Sam snarled, and Dean wasn't sure whether to be worried or relieved that he was finally starting to show some emotion. "Look, I'm sure there are some creatures you need to kill, so why don't you get back to hunting now that you've fulfilled your big-brotherly obligation? No need to stay here wasting time on me anymore."

"Wasting time? We're supposed to be a team, Sam. If one of us needs some down time, we both take it. That's just how it works."

"Don't do that," Sam snapped, his eyes suspiciously wet even though his teeth were clenched tight in anger. "Don't play the whole, 'We're a team,' card just to try and make me feel better; you don't even mean it."

"What kind of crazy crap are you on? Of course I mean it, Sam! Why would I lie about that?"

"You're the one who said you were through with me a year and a half ago, Dean, not the other way around. I only stopped answering the phone after you made it clear you had nothing good to say to me. And we both know you're only here now because you needed another person for that hunt, so don't try to make it mean any more than that."

Dean sighed, biting his lip hard as he debated whether or not to tell Sam what he'd been dying to say since he got to Palo Alto. The way things were going now, it seemed there would be no other choice. His brother obviously still held a very misplaced grudge against him, and Dean couldn't allow it to continue any longer. "Sam, we need to talk about something."

"You think?" the younger Winchester asked, crossing his arms but listening to Dean all the same.

"There's… There's something I've been meaning to tell you for a really long time, and I just never got the chance. I, uh… I actually knew Jess for a while before this whole thing."

"…What?"

"Yeah," he continued, fiddling with the amulet around his neck nervously. "Three days after you broke your leg and had to have surgery, she called me, told me about the text you'd gotten that upset you so bad. She chewed me out but good, couldn't believe I'd say that stuff to my own brother, and the whole time I had no freaking clue what she was talking about. It took a while before she calmed down and told me, and when she did… I just couldn't believe it. I'd spent that whole night trying to send you a message on your birthday, but it kept getting bounced back at me and I finally just gave up. I had no idea you'd ever gotten another text from my phone, Sam."

"Then… who sent the first one?" Sam's defenses were starting to crumble, his hands trembling as the anger at Dean he'd held all these years began to slip away against his will.

"It was Dad. He was pretty drunk that night, and when I went out to get food I guess he sent you that message so you'd think it was me. When I found out, I punched him straight in the jaw. He didn't even get mad; he must've known what it was for, seemed like he felt pretty shitty about it afterward." He chuckled, a bitter and resentful sound reserved especially for those moments when he knew John had failed both of them as their parent. "But I didn't know, and by the time I did you wouldn't talk to me anymore. I don't blame you, but I wish I could've fixed it before we got to this point."

"Oh, God. Dean, I…" Sam stammered, and Dean could practically see guilt over this new development rising up within him to join the survivor's guilt he already carried. "I'm so sorry, I didn't know or I would've…"

He trailed off, face crumpling, and Dean watched his head bow until his shaggy brown hair completely obscured his face. His shoulders hitched once, and then again, and when he spoke his voice wavered so badly that Dean imagined it probably hurt to talk.

"I miss her. I miss her so much, Dean…"

Dean's heart broke for his little brother, who he'd hoped would never have to feel the kind of anguish he and John had experienced with Mary's loss. He strode forward and wrapped his arms around Sam, feeling the younger man relax immediately as he sank against his big brother and shook with breathless sobs. His knees wobbled terribly, and Dean gently pulled them both down to sit on the floor, Sam never leaving his brother's comforting embrace or removing his head from his shoulder.

"Jess was a great girl, Sammy," he said softly, slowly rubbing a hand up and down the younger man's back when he began to cough softly into Dean's shoulder. "I know it doesn't help much, but even I could tell how crazy she was about you after just two minutes on the phone with her. And all of this… I'm sorry. God, Sammy, you have no idea how sorry I am."

"Not… your fault…"

"I know, but I couldn't protect you from this, and I wish so much that I could have."

Sam sniffed, his next words a choked whisper. "Me, too…"

They stayed like that for a while longer, Dean slowly rocking the two of them back and forth while Sam let himself feel the grief and anger and pain he'd been bottling up for far too long. He clung to his older brother like a lifeline and Dean clung back, not willing to let him drift away to drown alone in this sea of overwhelming emotion.

When at last Sam had finally calmed enough to loosen his grip on Dean, the older Winchester pushed away a little, smiling reassuringly at Sam's look of confusion and retrieving a few sheets of toilet paper from the small, dingy bathroom.

"Here," he said with a teasing grin. "Wipe your face before your makeup starts to run."

Sam smirked and punched his arm, sniffing a couple of times and wiping his eyes on the thin paper. "You're gonna tease me about this chick-flick moment forever now, aren't you?"

"No," Dean said calmly. "Never." At Sam's stunned expression, he chuckled and shrugged, making his way back to the kitchenette and retrieving his now cold and soggy burger to eat. After one bite, though, he grimaced and threw the rest in the trash. "All right, well, that tastes like old shoe. I'm gonna go get some takeout at the place down the street."

"The Golden Dragon," Sam offered, knowing exactly which place Dean was talking about; it had been his and Jessica's favorite Chinese takeout restaurant in all of Palo Alto. "They have great cream cheese wontons."

"Is that a request for food I hear?" Dean asked, relieved that Sam was finally going to eat something.

"Yeah. Unless you want me to go too. Otherwise, I think I'll shower. I've been smelling something bad all night, and…" He raised his arm and sniffed quickly, recoiling with a grimace. "Yep, it's definitely me."

Dean laughed. "Yeah, I'll get a little bit of all our usual stuff. Go clean up, Pigpen."

Sam nodded, and Dean waited until he'd gone into the bathroom and shut the door before he grabbed the keys to the Impala and locked the motel room door behind him. He couldn't help the smile that crept across his lips as he drove off in search of late-night Chinese food. Sam might be hurting, but at least now he knew he could still always count on his big brother whenever times got tough. And come Hell or high water, that wasn't about to change.


End file.
